Have a look at www.bikely.com many people have posted rides in both cities which are either/ both challenging and enjoyable. I know there are a number of routes on there from Hornsby in northern sydney most of which involve lots of riding through national parks and rural areas (and lots of good hills). Another option would be to take a train to a gateway point and ride from there.
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Melbourne has a lot of off-road wonderful bike tracks. Easiest way to get onto them is to pop into a bike shop and buy the little booklet that describes them - around $25 or so last I looked. Also Google bike clubs for day rides.

Melbourne tends to be a bit more bike friendly though I don't fancy your chances of fining any vineyards too close to either Sydney or Melbourne city. To get a head start for cycle routes and trips, the bicycling organisations for each respective will be able to help.

Both (BNSW) Bicycle New South Wales and (BV) Bicycle Victoria are listed on this site under the Cycling Organisations and BUGs page. In addition, the (RTA) Roads and Traffic Authority, which deal with all the streets and transport, may be able to provide you with some good cycling routes.

For both Sydney and Melboune, both cities are quite large with a big urban sprawl. Sydney area takes up (for example) 100 km (North / South) by 50km (East / West). You need to do a bit of riding to get out as Sydney has the Blue Mountains inland which is a natural barrier. Once you make the trek up there you will start finding some townships. Have a look on Google Maps as there is a lot of hard riding involved. The nearest vineyard area is the Hunter Valley (next to Cessnock) up north. It is possible to reach via the scenic old pacific highway road which is none the less challenging and will take (depending on speed) over half a day. The Hunter Valley is nice and most wineries have open cellar doors from about 9am to 6pm and they are fairly close to one another (key word Pokolbin).

Well, I can't say I know any of this first hand, but there ARE some good winereies around Melbourne. Though most at least an hour+ drive out of the city, so it'll be a good thirst/appetite inducing ride. Could be done though, but I'm not clear on bike routes out of the city. As someone mentioned, there's probably a bike route map available for this.

On a side note, the regional freeways do permit bikes, since they're less traffic laden, and are a great smooth ride, just watch out for the occasional road trains (i.e., huge double-rig trucks) that are probably the most dangerous vehicles to cyclists on the freeway. Or if you want even less traffic, more countryside, the older back roads along the freeways are ideal, though narrower, a longer ride, and slightly less smooth riding.

For an alternative to travelling out of Melbourne, and if you want to get to the surrounding smaller cities/towns, the V-Line train services (the regional train network) are usually very good about bringing your bikes on to the train. As long as you keep it out of the way, i.e., not obstructing the doors/passge and prefereably avoid the peak services (7-9 am arriving at Melbourne, and 4-6pm LEAVING Melbourne), you'll have no trouble. So if you want to leave the city and base yourself out of town for a few days, the train can bring you to a regional centre like Ballarat, Traralgon, etc, from where you can cycle to surrounding country towns, or visit the local wineries at your leisure.
http://www.vline.com.au

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